Stereoselective synthesis of functional derivatives of 2-(2-carboxyethyl)pyrrolidine-2-carboxylic acid

Azomethine ylides generated from dimethyl 2-(arylmethylideneamino)pentanedioates by the action of AgOAc and Et3N reacted with dipolarophiles in regio- and stereoselective fashion to form 5-aryl-2-(2-carboxyethyl)pyrrolidine-2-carboxylic acid derivatives. 1,3-Dipolar cycloaddition of divinyl sulfone to the azomethine ylide generated from the Schiff base derived from methyl (S)-2-phthalimido-4-oxobutanoate and dimethyl glutamate gave chiral simplified kaitocephalin analogs.